4-(((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)butanoic acid | 1258196-95-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 4-(((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)butanoic acid
• 英文别名: 4-[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxybutanoic acid
• CAS: 1258196-95-0
• 化学式: C₁₆H₂₄O₁₀
• 分子量: 376.361
• InChiKey: GQADIPJUYVOKAM-NDDJGINWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-(((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)butanoic acid 在 5%-palladium/activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 4’-(2-oxo-2-((2-(4-(((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)butanamido)ethyl)amino)ethoxy)-[1,1‘-biphenyl]-3-carboxylic acid
  参考文献：
  名称：

  [EN] COMPOUNDS AND THERAPEUTIC USES THEREOF
  [FR] COMPOSÉS ET LEURS UTILISATIONS THÉRAPEUTIQUES

  摘要：

  本发明涉及具有将免疫应答与病原体连接起来的新化合物，以及在由感染性因子介导和/或引起的疾病或紊乱中使用该类化合物，包含该类化合物的组合物，其制备方法以及在该方法中使用的新中间体。

  公开号：

  WO2018203087A1
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 在 ruthenium trichloride 、 sodium periodate 、 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 4-(((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)butanoic acid
  参考文献：
  名称：

  Synthesis of a Single-Molecule l-Rhamnose-Containing Three-Component Vaccine and Evaluation of Antigenicity in the Presence of Anti-l-Rhamnose Antibodies

  摘要：

  Carbohydrates are generally considered to be poorly immunogenic. Therefore, new approaches for enhancing their immunogenicity are important for the development of carbohydrates as vaccine components. We hypothesized that conjugation of an L-rhamnose (Rha) moiety to a carbohydrate antigen would enhance the antigenicity of the antigen in mice possessing anti-Rha antibodies via an antibody-dependent antigen uptake mechanism. To explore this hypothesis, we synthesized a single-molecule three-component vaccine containing the GalNAc-O-Thr (Tn) tumor-specific antigen, a 20 amino acid helper T-cell epitope (YAF) derived from an outer-membrane protein of Neisseria meningitides, and a Rha moiety. The vaccine was synthesized by automated Fmoc-based solid-phase peptide synthesis and deacetylated by brief treatment with NaOMe. Groups of female BALB/c mice were immunized and boosted with Rha-ovalbumin (Rha-OVA) formulated with either TiterMax Gold or Sigma Adjuvant System for a period of 35 days in order to determine optimal conditions for generating anti-Rha titers in mice. Anti-Rha antibody titers were > 100 fold higher in groups of mice immunized with Rha-OVA than in the control groups. Mice producing anti-Rha were challenged with Rha-YAF-Tn or YAF-Tn. Sera collected from the groups initially immunized with Rha-OVA and later challenged with Rha-YAF-Tn showed a 2-fold increase in anti-Tn titer at 1/100 serum dilution relative to mice not immunized with Rha-OVA. An in vitro T-cell proliferation study using cells primed with either Rha-YAF-Tn or YAF-Tn was done to examine possible differences in antigen uptake and presentation due to anti-Rha antibody and chemical modification. Proliferation of T cells was stimulated by a 10-fold lower antigen concentration in the presence of Rha antibodies. The results strongly suggest that T cells present in the spleen were presented with higher concentrations of Rha-YAF-Tn as a result of the presence of the anti-Rha antibodies.

  DOI：

  10.1021/ja107029z

文献信息

• <scp>l</scp>-Rhamnose-containing supramolecular nanofibrils as potential immunosuppressive materials
  作者：Fan Zhao、Balthasar A. Heesters、Isaac Chiu、Yuan Gao、Junfeng Shi、Ning Zhou、Michael C. Carroll、Bing Xu

  DOI：10.1039/c4ob01362j

  日期：——

  An L-rhamnose-based hydrogelator self-assembles to form nanofibrils, which, in contrast to the properties of monomeric L-rhamnose, suppress the antibody response of mice to phycoerythrin (PE), a fluorescent protein antigen. As the first example of the supramolecular assemblies of a saccharide to suppress immunity, this work illustrates a new approach of immunomodulation.

  一种基于L-兰醇糖的水凝胶剂自组装形成纳米纤维，与单体L-兰醇糖的特性相比，抑制了小鼠对荧光蛋白抗原藻红蛋白（PE）的抗体反应。作为首个抑制免疫的糖类超分子组装的例子，这项工作展示了一种新的免疫调节方法。
• COMPOUNDS AND THERAPEUTIC USES THEREOF
  申请人：Centauri Therapeutics Limited

  公开号：EP3619223A1

  公开（公告）日：2020-03-11
• NOVEL COMPOUNDS AND THERAPEUTICS USES THEREOF
  申请人：Centauri Therapeutics Limited

  公开号：US20200069767A1

  公开（公告）日：2020-03-05

  The invention relates to novel compounds with the ability to link an immune response to a pathogen, to the use of said compounds in a disease or disorder mediated and/or caused by an infective agent, to compositions containing said compounds, processes for their preparation and to novel intermediates used in said process.